Roofing & Siding Contractor in Highland, NY
Roofing & Siding Contractor in Highland, NY
- BBB Accredited A+
- 25+ Years in the Hudson Valley
- Free Estimates
- 5.0 stars on Google
SSKM Construction repairs and replaces roofs and siding in Highland, NY, the commercial center of the Town of Lloyd on the Hudson's west bank. From the riverfront near the Walkway Over the Hudson to the orchards toward Illinois Mountain, we keep Highland homes weather-tight. Every job starts with a free written estimate.
- How fast can you respond? Highland is about 25 minutes from our Newburgh shop.
- Near the river? Yes, including homes by the Walkway Over the Hudson and Franny Reese State Park.
- What does winter do to roofs here? Ice at the eaves and wind off the river are what we see most.
- Siding too? Yes. Roofing and siding handled as one weather-tight job.
Highland sits on the Hudson's west bank, where the Walkway Over the Hudson meets the Hudson Valley Rail Trail and apple orchards run up toward Illinois Mountain. SSKM Construction keeps Highland roofs and siding standing up to Hudson Valley winters, with a short drive up Route 9W from our Newburgh shop for fast estimates and storm response.
What We Do in Highland
Roofing, siding & construction in Highland
Roofing
All Roofing services →
Roof replacement
All Roof replacement services →
Roof repair
All Roof repair services →
Siding
All Siding services →
Decks
All Decks services →
Framing
All Framing services →
Remodeling
All Remodeling services →
Interior painting
All Interior painting services →Exterior painting
All Exterior painting services →
Snow removal
All Snow removal services →
Kitchen remodel
All Kitchen remodel services →Bathroom remodel
All Bathroom remodel services →One crew for all of it. Whichever of those you need, the visit and the written estimate cost you nothing.
Real Reviews
Rated 5.0 stars by Hudson Valley homeowners
The roof was completely done and cleaned up in 2 days, his guys had even cleaned out my gutters.
SSKM Construction did an outstanding job replacing the sheathing and removing and replacing the existing siding on my home.
It has been a pleasure and honor to work with Luis and his crew for the past 5 years.
Luis and his crew did a great job swapping out two nasty pull-out windows in my basement.
Those reviews are real, and they are on Google. If you would like to be the next one, the estimate costs nothing.
Local Conditions
Common roofing challenges in Highland, NY
- Riverfront homes exposed to wind off the Hudson near the Walkway Over the Hudson and Franny Reese State Park
- Aging roofs on older farmhouses scattered among the apple orchards outside the village center
- Ice dams and freeze-thaw damage from the same Hudson Valley winters we handle daily across the region
- Homes tucked into the slope toward Illinois Mountain, where roof pitch and drainage need extra attention
- A mix of century-old village homes and newer construction near the Route 9W corridor, each needing a different roofing approach
About Highland, Ulster County
Highland is the commercial center of the Town of Lloyd, sitting in Ulster County on the west bank of the Hudson River directly across from Poughkeepsie. The Mid-Hudson Bridge carries vehicle traffic across the river, while the Walkway Over the Hudson, the world's longest pedestrian bridge, spans the same crossing high above the water on the deck of the old 1888 Poughkeepsie-Highland railroad bridge. On the Highland side, the Walkway meets the Hudson Valley Rail Trail and Franny Reese State Park, and Illinois Mountain rises just inland.
The town has long been known for its apple orchards, and today it's a mix of riverfront homes, older village houses, and newer construction spreading out along Route 9W. That range of housing, from river-facing exposure to hillside lots, is exactly what we've built our roofing and siding experience around. Whether it's a village home a short walk from the Walkway or a newer build heading out toward the orchards, we treat each one on its own terms.
Need roofing or siding in Highland? Call (845) 549-7944 or request a free estimate.
Recognise any of that on your own house? We will come out, look at it properly, and tell you what it actually needs.
That is our patch. If your street is on that map, we can be out to look at the job this week.
Local Routes
How we get to Highland, NY
We work Highland out of Newburgh. These are the corridors that connect it to the neighbouring towns we cover, and the roads our trucks are actually on getting there.
We cover the rest of the mid-Hudson Valley from the same Newburgh shop: Roofing in Cornwall, Roofing in Newburgh, Roofing in Wappingers Falls, Roofing in Middletown.
Highland to Poughkeepsie
- Roads we run
- US 44, NY 55, US 9W
- County
- Dutchess County
- Straight-line distance
- About 2 miles, not a drive time
Highland to Hyde Park
- Roads we run
- US 9, US 44, NY 55
- County
- Dutchess County
- Straight-line distance
- About 4.5 miles, not a drive time
Highland to New Paltz
- Roads we run
- NY 299, US 9W, NY 32
- County
- Ulster County
- Straight-line distance
- About 6.6 miles, not a drive time
Straight-line miles between town centres, measured from OpenStreetMap coordinates on 27 August 2026. They are not drive times. Road names are the routes mapped between those same two points.
Good to Know
Roofing in Highland, from the riverfront to Illinois Mountain
Siding, seasonal planning, and serving Highland
Highland's housing runs from riverfront homes and older village houses near the Walkway Over the Hudson to newer construction spreading out toward Route 9W, and each carries its own siding needs. Older homes near the orchards often still have original wood or early vinyl siding that needs careful matching, while newer builds are usually already on vinyl or fiber-cement but due for an upgrade.
Either way, the details behind the panels are what actually keep water out: proper flashing at windows and doors, a continuous moisture barrier, and tight seams that hold up against wind coming off the river. Vinyl is the common value choice on newer homes, and modern insulated versions add real R-value against a Hudson Valley winter, though it can crack under impact in deep cold. Fiber-cement holds up better on exposed riverfront walls and carries paint far longer, which is worth the extra cost on a home that takes the wind straight off the water.
Given our winters, we schedule larger roof and siding jobs for the warmer months when sealants and adhesives cure properly. Storms don't wait for good scheduling, though, and a wind-damaged roof or active leak in Highland gets a fast response, with tarping and temporary repairs first and a permanent fix once conditions allow. SSKM Construction Corp serves Highland and the rest of Ulster County from our base in Newburgh, a short run up Route 9W, and we're glad to provide any Highland homeowner a free, no-pressure estimate for roofing or siding.
Honest, on time, and the finished work speaks for itself.
Why Highland homeowners choose SSKM
Highland homeowners get a contractor that already knows the roads and the roofs, not one driving in cold from another region. Our shop sits just down Route 9W in Newburgh, so we know the pull of a riverfront wind, the shade patterns on a hillside lot toward Illinois Mountain, and the age of the farmhouses scattered among the orchards. That familiarity, paired with more than 25 years in the trade, is what Luis and Steven have built their reputation on.
Because we self-perform roofing, siding, framing, decks, remodeling and painting, a Highland project that turns out to involve more than the roof doesn't become your job to coordinate. If we find rotted sheathing behind old siding or structural work under a failing roof, the same crew handles it, rather than you tracking down a second contractor.
For Highland homeowners, the decision comes down to trust, response time, and clear communication. We're insured, offer free estimates, and hold a 5.0-star rating on Google, so you can get an honest, no-pressure assessment of your roof, siding, or larger project from a crew that's never far away.
Still deciding? Tell us what the roof or the room is doing and we will come look at it. The estimate is free and written down.
At a Glance
SSKM Construction Corp in Highland, NY at a glance
| Where our crew comes from | North on Route 9W through New Windsor and Plattekill, about 25 minutes |
|---|---|
| Estimates | Free, and written down before any work starts |
| Google rating | 5.0 stars on Google |
| Years in the Hudson Valley | 25+ |
| Who you deal with | Luis and Steven, the co-owners, and the SSKM crew. Not a call centre |
| Trades under one roof | Roofing, roof replacement, roof repair, siding, decks, framing, remodeling, kitchen and bathroom remodels, interior and exterior painting, snow removal |
Ready to protect and improve your home?
Free estimates · 25+ years in the Hudson Valley · Mon-Sun 7:00 AM to 6:00 PM
Getting There
Getting to Highland from our shop
Highland is a straightforward trip from our shop on North Plank Road: north on Route 9W through New Windsor and Plattekill, with most of Highland, including the riverfront and the area around the Walkway Over the Hudson, about 25 minutes from our door.
Nearby Areas
Other towns we serve near Highland
Good to Know
Highland roofing: frequently asked questions
How fast can you respond to a roofing job in Highland?
Quickly. Highland is a straightforward run up Route 9W from our Newburgh shop, about 25 minutes, so an estimate or a storm repair is a short run for our crew.
Do you work on Highland homes near the river and the Walkway Over the Hudson?
Yes. The riverfront homes and the neighborhoods around the Walkway Over the Hudson and Franny Reese State Park are some of the areas we work in most often in Highland.
How does winter weather affect roofs in Highland?
Highland sees the same Hudson Valley winters we handle across the region: heavy snow load and freeze-thaw cycling that drives ice dams at the eaves. We check ventilation, insulation, and flashing so meltwater drains instead of backing up under shingles.
Can you handle storm damage in Highland?
Yes. Call (845) 549-7944 and we will get out to assess it. Wind off the river can crease or lift shingles without it being obvious from the ground, so we inspect the roof itself before quoting a fix.
Do you handle siding on the older Highland farmhouses near the orchards too?
We do. Highland's older farmhouses often carry original wood or early siding that needs careful matching, and we handle both the siding and the roof so the whole exterior gets sealed together.
We pull the permits our work needs and deal with the inspections. If you want to check the requirements yourself, Highland's building permits and inspections are handled by the town, and current requirements are listed on the Town of Lloyd official site.
Question we did not answer? Ask it on the phone. You will get a straight answer from an owner, not a script.
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